38573-88-5|1-Bromo-2,3-difluorobenzene| Ambeed

Structure of 2,3-Difluorobromobenzene
CAS No.: 38573-88-5

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Quality Control of [ 38573-88-5 ] Purity: 97% SDS Specification

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Product Details of [ 38573-88-5 ]

CAS No. :	38573-88-5
Formula :	C₆H₃BrF₂
M.W :	192.99
SMILES Code :	C1=CC=C(C(=C1F)F)Br
MDL No. :	MFCD00061136
InChI Key :	RKWWASUTWAFKHA-UHFFFAOYSA-N
Pubchem ID :	2733260

Safety of [ 38573-88-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 38573-88-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	34.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.06
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.57
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.91
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.15

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.3
Solubility	0.0967 mg/ml ; 0.000501 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.47
Solubility	0.658 mg/ml ; 0.00341 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.81
Solubility	0.0298 mg/ml ; 0.000155 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.48 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.48

Application In Synthesis of [ 38573-88-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 38573-88-5 ]

[ 38573-88-5 ] Synthesis Path-Downstream 1~41

1
[ 38573-88-5 ]
[ 169526-37-8 ]
(3aS,9aR)-2-(2,3-Difluoro-phenyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-ol [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 6923 - 6931.

2
[ 110-85-0 ]
[ 38573-88-5 ]
[ 876379-86-1 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3628 - 3635.
[2]Patent: WO2006/15737,2006,A1 .Location in patent: Page/Page column 57.
[3]Patent: WO2006/50976,2006,A1 .Location in patent: Page/Page column 35.

3
(RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile [ No CAS ]
tris(dibenzylideneacetone)dipalladium ⁽⁰⁾ [ No CAS ]
[ 38573-88-5 ]
(R,S)-3-[4-(2,3-difluorophenyl)piperazin-1-yl]-2-[(R,S)-(2-methoxyphenyl)(1-naphthyl)methyl]-2-methyl-3-oxopropanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate; In diethyl ether; toluene;	EXAMPLE 93 (R,S)-3-[4-(2,3-difluorophenyl)piperazin-1-yl]-2-[(R,S)-(2-methoxyphenyl)(1-naphthyl)methyl]-2-methyl-3-oxopropanenitrile (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile (471 mg, 1.14 mmol), <strong>[38573-88-5]2,3-difluorobromobenzene</strong> (200 mg, 1.04 mmol), sodium tert-butoxide (139 mg, 1.45 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.031 mmol), racemic BINAP (39 mg, 0.062 mmol), and toluene (3 mL) were combined in a Carius tube, vacuum degassed, placed under an argon atmosphere, sealed and heated to 80° C. overnight. The reaction was cooled, taken up in diethyl ether, filtered, washed with water, saturated aqueous sodium bicarbonate, brine, dried over MgSO4, filtered, evaporated, and purified on slica gel (10percent hexanes/CH2Cl2) to yield 280 mg of the title compound as an off-white crystal solid. mp 198-200° C.; 1H NMR 500 MHz (DMSO-D6): delta 7.98 (d, 1H, J=7.33 Hz), 7.86 (m, 2H), 7.79 (d, 1H, J=8.25 Hz), 7.54 (t, 1H, J=7.64 Hz), 7.42 (m, 2H), 7.23 (t, 1H, J=7.64 Hz), 7.12 (m, 2H), 7.08 (m, 1H), 7.00 (q, 1H, J=9.01 Hz), 6.79 (m, 2H), 6.01 (s, 1H), 4.01 (s, 3H), 3.73 (bs, 4H), 2.96 (bs, 4H), 1.64 (s, 3H) MS (ESI) m/z 526 ([M+H]+); Anal. calcd for C32H29F2N3O2.0.20H2O: C, 72.63; H, 5.60; N, 7.94. Found: C, 72.65; H, 5.58; N, 7.79.

References: [1]Patent: US2005/256132,2005,A1 .

4
[ 38573-88-5 ]
[ 5876-51-7 ]
5-(2,3-difluorophenyl)-1,3-benzodioxole [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 3844 - 3845.

5
(2-iodobenzyloxy)triisopropylsilane [ No CAS ]
[ 38573-88-5 ]
2,3-difluoro-2'[(triisopropylsilyl)oxy]methyl}-1,1'-biphenyl [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 3844 - 3845.

6
[ 90-14-2 ]
[ 38573-88-5 ]
1-(2,3-difluorophenyl)naphthalene [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 3844 - 3845.

7
[ 38573-88-5 ]
[ 934964-21-3 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3628 - 3635.

8
[ 38573-88-5 ]
[ 876379-85-0 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3628 - 3635.

9
[ 38573-88-5 ]
tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4,6,10⁽¹⁴⁾,11,15-hexaene-5-carboxylic acid {4-[4-(2,3-difluoro-phenyl)-piperazin-1-yl]-butyl}-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3628 - 3635.

10
[ 38573-88-5 ]
[ 705281-32-9 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 6923 - 6931.

11
[ 38573-88-5 ]
[ 705281-26-1 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 6923 - 6931.

12
[ 38573-88-5 ]
(2S,3aS,9aR)-2-(2,3-Difluoro-phenyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 6923 - 6931.

13
[ 38573-88-5 ]
[ 705281-38-5 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 6923 - 6931.

14
[ 38573-88-5 ]
Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,3-difluoro-phenyl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 6923 - 6931.

15
[ 38573-88-5 ]
4-(2-bromo-6-fluorophenoxy)-1-methylpiperidine [ No CAS ]
[ 790667-58-2 ]

Yield	Reaction Conditions	Operation in experiment
54%; 21%		Add slowly a solution of 1-methyl-piperidin-4-ol (2.98 g) in DMF (20 mL) into a suspension of sodium hydride (95percent) (0.72 g) in DMF (25 mL) at room temperature. Heat the mixture in an oil bath at 65°C. After 30 MIN., add 1-bromo-2-, 3-DIFLUORO-BENZENE (5.0 g) and stir at 65°C. After 2 hr. , partition the reaction mixture between water and ether, dry over ANHYDROUS sodium sulfate, and evaporate to give a yellow oil. Separate on a silica gel column (110 g, solvent: ether, ETHER-2M NH3 in methanol 19: 1,9 : 1) to obtain 4- (2-bromo-6-fluoro-phenoxy)-1-methyl-piperidine (4.06 g, 54percent yield) and the title compound (1.60 g, 21percent yield). Mass spectrum (electric spray) M/Z = 288 (M+L), 290 (M+2+1) ;1H NMR (CDC13) : 7.12 (m, 1H), 6.92 (m, 2H), 4.30 (m, 1H), 2.69 (m, 2H), 2.30 (s, 3H), 2.28 (m, 2H), 1.97 (m, 2H), 1. 89 (m, 2H).

References: [1]Patent: WO2004/94380,2004,A1 .Location in patent: Page 38.

16
(RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile [ No CAS ]
[ 38573-88-5 ]
(R,S)-3-[4-(2,3-difluorophenyl)piperazin-1-yl]-2-[(R,S)-(2-methoxyphenyl)(1-naphthyl)methy]-2-methyl-3-oxopropanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃;	(RR, SS)-3- (2-METHOXYPHENYL)-2-METHYL-3- (1-NAPHTHYL)-2- (PIPERAZIN-1- YLCARBONYL) PROPANENITRILE (471 mg, 1.14 MMOL), 2, 3-difluorobromobenzene (200 mg, 1.04 MMOL), sodium tert-butoxide (139 mg, 1.45 MMOL), tris (DIBENZYLIDENEACETONE) dipalladium (0) (28 mg, 0.031 MMOL), racemic BINAP (39 mg, 0.062 MMOL), and toluene (3 mL) were combined in a Carius tube, vacuum degassed, placed under an argon atmosphere, sealed and heated to 80°C overnight. The reaction was cooled, taken up in diethyl ether, filtered, washed with water, saturated aqueous sodium bicarbonate, brine, dried over MgS04, filtered, evaporated, and purified on slica gel (10percent hexanes/CH2CI2) to yield 280 mg of the title compound as an off-white crystal solid. MP 198-200°C ; 1H NMR 500 MHz (DMSO-D6): 8 7. 98 (d, 1 H, J=7.33 Hz), 7.86 (m, 2H), 7.79 (d, 1 H, J=8.25 Hz), 7.54 (t, 1H, J=7.64 Hz), 7.42 (m, 2H), 7.23 (t, 1H, J=7.64 Hz), 7.12 (m, 2H), 7. 08 (m, 1H), 7.00 (q, 1H, J=9.01 Hz), 6.79 (m, 2H), 6.01 (s, 1H), 4.01 (s, 3H), 3. 73 (bs, 4H), 2.96 (bs, 4H), 1. 64 (s, 3H) HAS (ESI) M/Z 526 ( [M+H] +) ; Anal. calcd for C32H29F2N302 E 0. 20 H20 : C : 72. 63 H: 5.60 N : 7.94 Found : C: 72. 65 H: 5. 58 N : 7. 79.

References: [1]Patent: WO2004/99150,2004,A2 .Location in patent: Page 93-94.

17
[ 845868-17-9 ]
[ 38573-88-5 ]
[ 845868-18-0 ]

Yield	Reaction Conditions	Operation in experiment
24%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 20℃; for 4h;	Example 33 [0128] (4-(2-(2, 3-DIFLUOROPHENYL) ETHYNYL)-1-BOC-PYRROL-2-YL) (PYRROLIDIN-1- yl) methanone. A mixture of (4-ethynyl)-1-BOC-pyrrol-2-yl) (pyrrolidin-1-yl) methanone (4 g, 13. 88 mmol), 2, 3-DIFLUORO-1-BROMOBENZENE (4 g, 20.8 mmol), PDCL2PPH2 (0.97 g, 1. 38 mmol) and Cul (0.53 g, 2.76 mmol in trietylamine (40 ML) was stirred at room temperature for 4 hr. The solid was filtered and washed with ethyl acetate (100 mL). The filtrate was washed with 2N HC1 (3x 100 mL), brine (100 mL) and water (100 mL). The organic layer was dried and concentrated under reduced pressure. The crude product was purified by Biotage HPFC system (40-65percent EtOAC/Hexane) to afford title as a dark brown oil (1.35 g, 24percent).

References: [1]Patent: WO2005/16920,2005,A1 .Location in patent: Page/Page column 45.

18
[ 869554-72-3 ]
[ 38573-88-5 ]
N,N-diethyl-2',3'-difluoro-5-propylbiphenyl-2-carboxamide [ No CAS ]

References: [1]Patent: JP2005/350455,2005,A .Location in patent: Page/Page column 16.

Yield	Reaction Conditions	Operation in experiment
		Examples of the fluoroarylhalide represented by General Formula (5) specifically include...1-iodo-2,4,6-trifluorobenzene,1-chloro-3,4,5-trifluorobenzene,1-bromo-3,4,5-trifluorobenzene,1-iodo-3,4,5-trifluorobenzene, 1-chloro-2,3-difluorobenzene,1-bromo-2,3-difluorobenzene, 1-iodo-2,3-difluorobenzene,1-chloro-2,4-difluorobenzene, 1-bromo-2,4-difluorobenzene,1-iodo-2,4-difluorobenzene, 1-chloro-2,5-difluorobenzene,1-bromo-2,5-difluorobenzene, 1-iodo-2,5-difluorobenzene,...

20
[ 38573-88-5 ]
[ 388116-27-6 ]
[ 442562-83-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 70℃;Inert atmosphere;	Step 2 4-(2,3-Difluoro-phenyl)-1H-indole 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 6b (1.22 g, 5 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium hydroxide solution (7 ml, 2 mol/L) under an argon atmosphere. Upon completion of the addition, the reaction system was stirred at 75° C. in an oil bath overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 ml*3). The combined organic extracts were washed with saturated brine (10 ml), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(2,3-difluoro-phenyl)-1H-indole 6c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4 [M-1]
70%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃;Inert atmosphere;	4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 6b (1.22 g, 5 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium hydroxide solution (7 ml, 2 mol/L) under an argon atmosphere. Upon completion of the addition, the reaction system was stirred at 75°C in an oil bath overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 ml.x.3). The combined organic extracts were washed with saturated brine (10 ml), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(2,3-difluoro-phenyl)-1H-indole 6c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]
70%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃;Inert atmosphere;	4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 3b (1.22 g, 5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring under an argon atmosphere, and <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) and 7 mL of sodium hydroxide solution (2M) were then added to the solution. Upon completion of the addition, the reaction system was stirred at 75°C in an oil bath overnight. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 mL*3). The combined organic extracts were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give the title compound 4-(2,3-difluoro-phenyl)-1H-indole 3c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]

70%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 75℃;Inert atmosphere;	Step 2 4-(2,3-difluoro-phenyl)-1H-indole 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 3b (1.22 g, 5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring under an argon atmosphere, and <strong>[38573-88-5]1-bromo-2,3-difluoro-benzene</strong> (0.97 g, 5 mmol), tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) and 7 mL of sodium hydroxide solution (2M) were then added to the solution. Upon completion of the addition, the reaction system was stirred at 75° C. in an oil bath overnight. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 mL*3). The combined organic extracts were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give the title compound 4-(2,3-difluoro-phenyl)-1H-indole 3c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]
2.92 g (82%)	With nitrogen;Pd(PPh3)4; palladium; In tetrahydrofuran; water; ethyl acetate;	Example A-26 4-(2,3-Difluoro-phenyl)-1H-indole To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (3.78 g, 15.5 mmol), and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (3 g, 15.5 mmol) in THF (55 mL) were added Palladium catalyst Pd(PPh3)4 (0.54 g, 0.47 mmol) and the freshly prepared sodium hydroxide solution (1.865 g, 47 mmol in 22 mL of water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 75° C. oil bath for overnight. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed with brine, and dried over Na2SO4. After filtration, the solvents were evaporated, and the crude product was purified by a silica gel column to give 2.92 g (82percent) of 4-(2,3-difluoro-phenyl)-1H-indole.

References: [1]Patent: US2010/75952,2010,A1 .Location in patent: Page/Page column 47.
[2]Patent: EP2157093,2010,A1 .Location in patent: Page/Page column 39.
[3]Patent: EP2179998,2010,A1 .Location in patent: Page/Page column 14; 15.
[4]Patent: US2010/160317,2010,A1 .Location in patent: Page/Page column 14.
[5]Patent: US2003/69297,2003,A1 .

21
[ 251366-38-8 ]
[ 38573-88-5 ]
[ 251367-82-5 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; ammonium chloride; In tetrahydrofuran;	Example 48 2-Trifluoroacetamido-3-phenyl-6-(2,3-difluorobenzoyl)-imidazo[1,2-a]pyridine To a solution of <strong>[38573-88-5]2,3-difluorobromobenzene</strong> (471 ml, 4.206 mmol) in dry THF (20 mL) was added a solution of n-butyl lithium (1.6M in hexanes, 2.63 mL) at -78° C. The resulting yellow solution was stirred at the same temperature for 70 minutes, then a solution of 2-trifluoroacetamido-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (0.500 g, 1.28 mmol) in dry THF (20 mL), was added dropwise via a cannula. The red-orange solution was allowed to warm over 60 minutes. Saturated NH4Cl was added and the mixture was stirred for 25 minutes before extracting with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated in vacuo and purified by column chromatography (CH2Cl2/CH3CN 4/1) to give 390 mg of an orange solid. (69percent). MS(FAB), NMR.

References: [1]Patent: US6358971,2002,B1 .

22
6-Chloro-N-methoxy-N-methyl-nicotinamide [ No CAS ]
[ 38573-88-5 ]
[ 251366-35-5 ]

Yield	Reaction Conditions	Operation in experiment
130 mg (77%)	With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane; ethyl acetate;	Preparation 149 2-Chloro-5-(2,3-difluorobenzoyl)pyridine To a solution of <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (0.114 g, 0.746 mmol) in 3 ml of dry THF was added, at -78° C., n-butyl lithium (1.6 M in hexane, 0.47 ml, 0.749 mmol). The reaction mixture was stirred at this temperature for 1 hour. A solution of 6-chloro-N-methoxy-N-methyl-nicotinamide (0.13 g, 0.68 mmol) in 5 ml of THF was added and the reaction mixture was allowed to warm to RT and stir for 6 hours. Saturated NH4Cl was added and the mixture was extracted with CH2Cl2 (3*10 ml). The organic layers were combined, washed with brine, and dried over NaSO4. The solvents were removed in vacuo and the residue was purified by column chromatography (Hex/AcOEt 9:1) to give 130 mg (77percent) of an oily product. IR, NMR.

References: [1]Patent: US6358971,2002,B1 .

23
[ 38573-88-5 ]
[ 179894-36-1 ]
[ 179894-86-1 ]

Yield	Reaction Conditions	Operation in experiment
16 mg (62%)		EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).
16 mg (62%)		EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1 H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).
16 mg (62%)		EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1 H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).

References: [1]Patent: US5688810,1997,A .
[2]Patent: US5693646,1997,A .
[3]Patent: US5696130,1997,A .

24
trans-4-propylcyclohexylcyclohexenone [ No CAS ]
[ 38573-88-5 ]
1-(trans-4-propylcyclohexyl)-4-(2,3-difluorophenyl)-4-hydroxycyclohexene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium sulfate; In diethyl ether;	Example 23 A solution of 6.0 g of <strong>[38573-88-5]2,3-difluorobromobenzene</strong> in 25 m of anhydrous diethyl ether was added dropwise under stirring at 10-15°C to 0.66 g of magnesium metal powder, followed by reaction at room temperature for one hour so that a Grignard reagent was formed. After 4.5 g of trans-4-propylcyclohexylcyclohexenone were added under stirring at -10 to 0°C to the thus-formed Grignard reagent, they were reacted at room temperature for additional 1 hour. After the completion of the reaction, diluted hydrochloric acid was added dropwise to the reaction mixture, followed by the extraction of the reaction mixture with diethyl ether. After the extract was washed with saturated NaCl, anhydrous sodium sulfate was added to dry the extract. The diethyl ether was distilled off under reduced pressure, whereby 1-(trans-4-propylcyclohexyl)-4-(2,3-difluorophenyl)-4-hydroxycyclohexene was obtained as a crude reaction product.

References: [1]Patent: EP571652,1993,A1 .

25
[ 38573-88-5 ]
[ 135270-08-5 ]
[ 329744-64-1 ]

References: [1]Journal of Fluorine Chemistry,2006,vol. 127,p. 643 - 650.

26
[ 38573-88-5 ]
[ 100-51-6 ]
[ 295376-29-3 ]
[ 1036724-55-6 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 4588 - 4590.

27
[ 38573-88-5 ]
[ 57260-71-6 ]
[ 1020092-62-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 70℃; for 1.5h;	In a sealed tube, <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (517 mg, 2.68 mmol) Pd2(dba)2 (2percent), BINAP (4percent), and sodium f-butoxide (386.4 mg, 4.02 mmol) were added to /V-Boc-piperazine (500 mg, 2.68 mmol) and the solids were dissolved in dry toluene (5 ml_). The mixture was stirred at 700C for 90 min., filtered over Celite.(R)., washing with etylacetate and the organic layer was evaporated under reduced pressure. The crude was purified by flash chromatography (40percent etylacetate in hexane) to give 7 as pail yellow solid (95percent yield): 1H NMR, 300MHz, (CDCI3) delta 1.38 (s, 9H), 2.91 (m, 4H),3.48 (m, 4H), 6.55 (m, 1 H), 6.66 (m, 1 H), 6.83 (m, 1 H). ESI-MS m/z 321 [M+Na+], 221 , 199. Anal (Ci5H20F2N2O2) C, H, N.

References: [1]Patent: WO2008/43839,2008,A1 .Location in patent: Page/Page column 10; 13.

28
[ 38573-88-5 ]
[ 156682-53-0 ]
[ 2040-89-3 ]

References: [1]Synlett,2009,p. 633 - 637.

29
[ 1190363-23-5 ]
[ 38573-88-5 ]
[ 1190363-24-6 ]

Yield	Reaction Conditions	Operation in experiment
21%		6-(2,3-Difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-6-ol. In an oven-dried 500 mL round-bottomed flask was BuLi (17.19 mL, 43.0 mmol) in THF (100 mL) to give a colorless solution at -78° C. under nitrogen. 1-Bromo-2,3-difluorobenzene (4.81 mL, 43.0 mmol) was added dropwise via syringe. The mixture was stirred at -78° C. for 20 min, and 8,9-dihydro-5H-cyclohepta[b]pyridin-6(7H)-one (4.947 g, 30.7 mmol) (azeotroped with dry benzene and dried under high vac) dissolved in 10 ml THF was added dropwise via canuula (plus 10 ml THF rinse). The mixture was warmed up to rt in 1 h. TLC showed some conversion to a slightly more polar spot. After quenched with saturated NH4Cl solution, THF was stripped off. The remaining mixture was partitioned between water and EtOAc. The layers were separated and the organic layer was washed with brine, dried with Na2SO4, and concentrated to a dark oil. The residue was purified by FCC up to 10percent MeOH/CH2Cl2 (very difficult separation). The impure fractions were pooled and purified by FCC with EtOAc/CH2Cl2 up to pure EtOAc. The recoverd SM: 1.88 g (38percent). The product fractions were pooled and concentrated to a tan solid, which were washed repeatedly with Et2O to a tan solid (1.79 g, 21percent). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.27 (dd, J=4.91, 1.38 Hz, 1H) 7.38-7.47 (m, 1H) 7.30-7.35 (m, 1H) 6.97-7.12 (m, 3H) 3.93 (dd, J=14.60, 2.52 Hz, 1H) 3.06-3.20 (m, 2H) 2.86 (dd, J=14.60, 1.76 Hz, 1H) 2.37-2.68 (m, 2H) 1.68-1.94 (m, 2H) 1.17 (t, J=7.05 Hz, 1H).

References: [1]Patent: US2009/258866,2009,A1 .Location in patent: Page/Page column 26.
[2]Journal of Organic Chemistry,2017,vol. 82,p. 3710 - 3720.

30
[ 38573-88-5 ]
[ 62-53-3 ]
[ 1187856-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); In toluene; at 110℃;Inert atmosphere;	Example 1.18: Preparation of 2-(((lr,4r)-4-(((2,3- Difluorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetic Acid (Compound 51).; Step A: Preparation of 2r3-Difluoro-lambda'-phenylaniline.; A mixture of l-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong> (0.232 mL, 2.073 mmol), aniline (0.208 mL, 2.280 mmol), Pd2(dba)3 (95 mg, 0.104 mmol), BINAP (194 mg, 0.311 mmol), sodium tert- butoxide (299 mg, 3.11 mmol), and toluene (3 mL) in a sealed vessel under argon was heated in an oil bath at 110 0C overnight. The reaction mixture was filtered through a plug of celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give the title compound as a light brown oil (411 mg). LCMS m/z = 206.1 [M+H]+; 1H NMR (400 MHz, Methanol-^) delta ppm 6.53-6.64 (m, IH), 6.80-6.88 (m, 2H), 6.88-6.95 (m, IH), 6.95- 7.03 (m, 2H), 7.11-7.19 (m, 2H).

References: [1]Patent: WO2009/117095,2009,A1 .Location in patent: Page/Page column 136.

31
[ 74912-33-7 ]
[ 38573-88-5 ]
[ 1190363-06-4 ]

Yield	Reaction Conditions	Operation in experiment
55.3%		5-(2,3-difluorophenyl)nona-1,8-dien-5-ol. In an oven-dried 250 mL round-bottomed flask (t=g) was added 1-Bromo-2,3-difluorobenzene (2.304 mL, 20.58 mmol) in THF (60 mL) to give a colorless solution. After cooling to -78° C., BuLi (8.23 mL, 20.58 mmol) was added dropwise via syringe. The mixture was stirred at -78° C. for 20 minutes, and nona-1,8-dien-5-one (2.37 g, 17.15 mmol) (azeotroped with dry benzene) was added dropwise via canuula (plus 6 ml THF rinse). The mixture was warmed up to room temperature over 1 hour. Quenched with water and the THF solvent was stripped off. The remaining mixture was extracted with EtOAc. The layers were separated and the organic layer was washed with brine, dried with Na2SO4, and concentrated to a yellow oil. The residue was purified by FCC up to 35percent Et2O/hexane. The desired fractions were pooled and concentrated to the product as a colorless oil (2.39 g, 55.3percent). 1H NMR (400 MHz, CDCl3) delta 7.30-7.22 (m, 1H), 7.10-7.03 (m, 2H), 5.82-5.70 (m, 2H), 4.97-4.85 (m, 4H), 2.20-2.00 (m, 4H), 2.00-1.75 (m, 4H).

References: [1]Patent: US2009/258866,2009,A1 .Location in patent: Page/Page column 21.
[2]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 337 - 341.

32
[ 1190363-45-1 ]
[ 38573-88-5 ]
[ 1190363-46-2 ]
[ 1397526-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate; 2-(dicyclohexylphosphino)-2'-methylbiphenyl;palladium diacetate; In toluene; at 80℃; for 20h;	(6S,9R)-6-(2,3-Difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one. See Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. In an oven-dried 1 L flask was Sodium tert-butoxide (13.19 g, 137 mmol), PALLADIUM(II) ACETATE (0.948 g, 4.22 mmol), and 2-(Dicyclohexylphosphino)-2'-methylbiphenyl (1.539 g, 4.22 mmol) weighed in a nitrogen bag. (R)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (35.21 g, 106 mmol), Toluene (106 mL) (degassed in the original bottle by nitrogen gas), and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (14.18 mL, 127 mmol) were added under nitrogen. The flask stirred at 80° C. in a pre-heated oil bath for 20 h. Volatiles were stripped off and the residue was partitioned between EtOAc (400 ml) and water (400 ml). The layers were separated. The aqueous layer was extracted with EtOAc (50 ml). The combined organic layer was washed with brine, dried and concentrated to a dark oil. It was passed through a plug of silica gel (loaded with CH2Cl2 and eluted with EtOAc/hexane up to 30percent EtOAc). The crude product was obtained as a dark red oil (86percent mass recovery),. 1H NMR showed approximately 6/1 ratio of the desired trans isomer to the cis isomer. MS(ESI)[M+H+]=446.21.
	With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 95℃; for 4h;Large scale;	4.2.1. First-generation strong base process. A mixture of toluene (14.9 L), 2 (3.50 kg, 18.1 mol), 1 (4.92 kg, 14.8 mol), palladium acetate (0.132 kg, 0.588 mol), tri-tert-butylphosphonium tetrafluoroborate (0.174 kg, 0.600 mol), and sodium tert-butoxide (1.88 kg, 19.6 mol) was heated to 95 °C for 4 h. The resulting dark mixture was cooled to 25 °C and diluted with ethyl acetate (44.5 L), washed with saturated ammonium chloride solution (224.7 L), phase split, and concentrated the organic to ~25 L under vacuum. The dark solution was absorbed onto a packed bed of alumina (19.8 kg) and eluted with toluene (203 L). The fractions containing 3 were combined and solvent swapped to IPA and concentration to 3 L/kg of 3. The IPA solution brought to 45 °C and water (1.5 L/kg) was added to the solution over 10 min, and the mixture seeded with 5 wt percent 3. The mixture was cooled to 40 °C over 2.5 h and water (1.5 L/kg) was added to the solution over 50 min. The resulting slurry was cooled to 25 °C over 1 h and aged for an additional 1 h followed by filtration. The cake was washed with a solution of IPA/water (1:1, 9.17 L) and dried under vacuum (at atmospheric pressure, 50 °C) for 24 h to afford 3 (4.15 kg, 63percent, 12:1 dr).

References: [1]Patent: US2009/258866,2009,A1 .Location in patent: Page/Page column 31.
[2]Organic Letters,2012,vol. 14,p. 4938 - 4941,4.
[3]Tetrahedron,2013,vol. 69,p. 5677 - 5684.

33
[ 38573-88-5 ]
C₆H₄C₆H₂F₂B(OH)2C₅H₁₁ [ No CAS ]
[ 1207506-98-6 ]

References: [1]Journal of Materials Chemistry,2010,vol. 20,p. 299 - 307.

34
[ 38573-88-5 ]
C₆H₄C₆H₂F₂B(OH)2C₅H₁₁CH₂CH₂ [ No CAS ]
[ 1207506-99-7 ]

References: [1]Journal of Materials Chemistry,2010,vol. 20,p. 299 - 307.

35
[ 1025699-99-3 ]
[ 38573-88-5 ]
[ 1217484-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; caesium carbonate;POPd; In water; N,N-dimethyl-formamide; at 150℃; for 0.166667h;Microwave irradiation;	In a 5mL microwave vial, methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)benzoate (250 mg, 0.71 mmol), l-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong> (273.2 mg, 1.416 mmol), cesium carbonate (1153 mg, 3.539 mmol), tetra-n-butylammonium iodide (261.4 mg, 0.7078 mmol), and POPd (35.51 mg, 0.07078 mmol) were dissolved in Water (0.5 mL, 30 mmol) and NN- dimethylformamide (3 mL, 30 mmol). The reaction mixture was microwaved for 10 mins at 150 degrees. The reaction mixture was extracted with ethylacetate and washedd repeatedly with brine. The solvent removed under reduced pressure and usedd in teh next reaction without further purification.

References: [1]Patent: WO2010/33168,2010,A2 .Location in patent: Page/Page column 93.

36
[ 1025699-99-3 ]
[ 38573-88-5 ]
[ 1217484-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; caesium carbonate;POPd; In water; N,N-dimethyl-formamide; at 150℃; for 0.166667h;Microwave irradiation;	Into a 5 mL microwave vial were charged with methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (250 mg, 0.71 mmol), l-bromo-2,3- difluorobenzene (273 mg, 1.42 mmol), cesium carbonate (1.15 g, 3.54 mmol), tetra-n-butylammonium iodide (261 mg, 0.71 mmol), POPd (35 mg, 0.071 mmol), water (0.5 mL) and NN-dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150 0C for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to give the residue which was purified by silica gel column to yield the title compound.

References: [1]Patent: WO2010/33168,2010,A2 .Location in patent: Page/Page column 78.

37
[ 38573-88-5 ]
[ 927-74-2 ]
[ 939043-50-2 ]

Yield	Reaction Conditions	Operation in experiment
	bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 20 - 65℃; for 20h;	Intermediate 25; 4-(2,3-Difluorophenyl)-3-butyn-1-ol; To a solution of <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10.0 g, 51.82 mmol, Aldrich) in dimethylamine (200 ml) under nitrogen were added Bis(tripheylphenylphosphine)palladium(II) dichloride (0.73 g, 1.037 mmol), copper(I) iodide (0.1 g, 0.525 mmol) and 3-butyn-1-ol (11.76 ml). The temperature was raised from ambient to 65° C. and held there with stirring for 20 h, after which the mixture was cooled and all volatiles removed by rotary evaporation. The residue was partitioned between a mixture of 2N HCl (400 ml), brine (100 ml) and dichloromethane (400 ml). A second 100 ml dichloromethane extract and the layers were separated and aqueous was washed with DCM (100 ml). Extracts were combined and the mixture passed through a hydrophobic frit and evaporated under reduced pressure to give a dark brown oil. This oil was purified using a CombiFlash.(R). Companion.(R). 330 g Redisep.(R). silica column eluting with a gradient of cyclohexane:ether (0 to 100percent) affording the title compound as a light orange oil (9.149).H.p.l.c. Rt=2.76 min.1H nmr (CDCl3) delta: 1.88 (1H, t), 2.75 (2H, t), 3.86 (2H, q), 7.01 (1H, m), 7.10 (1H, m), 7.17 (1H, m).

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1588 - 1592.
[2]Patent: US2008/306045,2008,A1 .Location in patent: Page/Page column 21.

38
[ 38573-88-5 ]
[ 203661-69-2 ]
[ 1225276-78-7 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 2-(2,3-difluorophenyl)-7-azaspiro[3.5]nonane hydrochloride; To a solution of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (2.48 g, 10.36 mmol) in THF (50 mL) at 0° C. was added 2,3-difluorophenylmagnesium bromide (prepared from stirring <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (4.00 g, 20.73 mmol) and isopropyl magnesium chloride (15.7 mL, 20.4 mmol) in THF (10 mL) at r.t. for 14 hrs). After 1 h, the reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layers were dried over sodium sulfate, filtered, and concentrated to give the crude alcohol as a pale yellow oil. A solution of the crude alcohol and triethylsilane (7.0 mL, 44.0 mmol) in methylene chloride (50 mL) was treated with borontrifluoride diethyl etherate (2.56 mL, 20.7 mmol) and trifluoroacetic acid (3.9 mL, 52.0 mmol) at 0° C. After 1 h at 0° C., the reaction was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The oil was diluted with ether and treated with 4N HCl/dioxane (4 mL). The precipitate was filtered and dried to give the title compound as a white solid (1.5 g, 61percent).

References: [1]Patent: US2010/113465,2010,A1 .Location in patent: Page/Page column 26.

39
[ 38573-88-5 ]
[ 21743-25-9 ]
1-(dimethylphosphanyl)-2,3-difluorobenzene [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 1859 - 1861.

40
[ 1069-08-5 ]
[ 38573-88-5 ]
[ 1219134-59-4 ]

Yield	Reaction Conditions	Operation in experiment
94%		To a solution of <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (5.0 g, 25.9 mmol) in ether (50 ml_) was added n-Bu (17.00 mL of 1.6 M n-BuLi hexene solution, 27.2 mmol) dropwise over 1 hour at -780C. The reaction was stirred for an additional hour at -780C then Et2NPCI2 (2.3 g, 13.0 mmol) in ether (20 mL) was added drop wise over 30 minutes resulting in purple coloured slurry. The reaction was allowed to warm to room temperature overnight. Volatiles were removed in vacuo and the residue was extracted with toluene (3 x 10 mL) and the solution was pumped to dryness. The product was isolated without further purification yielding a purple oil (4.0 g, 94percent). 1H NMR (delta, CD2CI2): 7.24-7.02 (m, 6H), 3.07 (d of q, 4H, JPH = 13 Hz, JHH = 7 Hz), 0.97 (triplet, 6H, JHH = 7 Hz). 19F NMR (6,CD2CI2): -132.88 (d of m, J = 42 Hz), -140.35 (m).

References: [1]Patent: WO2010/34101,2010,A1 .Location in patent: Page/Page column 23.

41
[ 398489-26-4 ]
[ 38573-88-5 ]
[ 1227617-37-9 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 8; TERT-BUTYL S-^1S-DIFLUOROPHENYL)-S-HYDROXYAZETIDINE-I - CARBOXYLATE; To a solution of 3-bromo-1 ,2-difluorobenzene (2.3 g, 11.8 mmol) in dry diethylether (20 ml) at -78°C, under nitrogen was added n-butyllithium (2.5 M in hexane, 4.7 ml, 11.8 mmol) dropwise. The mixture was stirred for 1 h after which a solution of 1-Boc-3-azetidinone (2.0 g, 11.7 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at -78°C for 15 min and then brought to ambient temperature and stirred for 2 h. Aqueous ammonium chloride (50 mL, 50percent) and diethylether was added, the organic phase was collected and the aqueous phase was extracted with ethyl acetate (2x50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1 :4 to 1 : 1 ) to give the title compound (1.9 g). MS m/z (rel. intensity, 70 eV) 285 (M+, 1 ), 156 (55), 141 (69), 127 (bp), 57 (88).
		Preparation 1TERT-BUTYL 3-(2,3-DIFLUOROPHENYL)-3-HYDROXYAZETIDINE-1 - CARBOXYLATE 0 To a solution of 1 -<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong> (2.48 g, 12.86 mmol) in dry diethylether (40 ml) at -780C was added dropwise n-butyllithium (2.5 M in hexane, 5.1 ml, 12.86 mmol). The mixture was stirred for 30 min after which a solution of 1 -Boc- azetidone (2.0 g, 1 1 .69 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at -780C for 30 min and then brought to ambient 5 temperature and stirred for 1 h. Aqueous saturated ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (2x50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1 : 1 ) to give the title compound Yield: 1 .89 g. MS m/z (rel.0 intensity, 70 eV) 285 (M+, 1 ), 156 (68), 141 (40), 127 (63), 57 (bp).
		To a solution of <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (2.48 g, 12.86 mmol) in dry diethylether (40 ml) at -78° C. was added dropwise n-butyllithium (2.5 M in hexane, 5.1 ml, 12.86 mmol). The mixture was stirred for 30 min after which a solution of 1-Boc-azetidone (2.0 g, 11.69 mmol) in dry diethyl ether (20 mL) was added dropwise. The resulting mixture was stirred at -78° C. for 30 min and then brought to ambient temperature and stirred for 1 h. Aqueous saturated ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (2.x.50 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane 1:1) to give the title compound Yield: 1.89 g. MS m/z (rel. intensity, 70 eV) 285 (M+, 1), 156 (68), 141 (40), 127 (63), 57 (bp).

References: [1]Patent: WO2010/58017,2010,A1 .Location in patent: Page/Page column 20.
[2]Patent: WO2010/58020,2010,A1 .Location in patent: Page/Page column 21.
[3]Patent: US2011/257148,2011,A1 .Location in patent: Page/Page column 9.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hunsdiecker-Borodin Reaction • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Passerini Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions of Dihalides • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 38573-88-5 ]

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A105757 [156682-52-9]

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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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CAS No.: 38573-88-5

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CAS No.: 38573-88-5

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CAS No.: 38573-88-5

Alternative Products

Product Details of [ 38573-88-5 ]

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Computational Chemistry of [ 38573-88-5 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

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Medicinal Chemistry

Application In Synthesis of [ 38573-88-5 ]

[ 38573-88-5 ] Synthesis Path-Downstream 1~41

Related Products

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Technical Information

Categories

Related Functional Groups of [ 38573-88-5 ]

Fluorinated Building Blocks

Aryls

Bromides

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Health hazards

Environmental hazards

Inquiry

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[ 38573-88-5 ]